m-Anisoyl chloride → 2-(3-Methoxybenzoylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide

HRID 45358

Reaction equation

HRID 45358 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH2:27])=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH:27][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 74374m-Anisoyl chlorideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 37138162-(3-Methoxybenzoylamino)-4-methylthiazole-5-carboxylic Acid BenzylamideYield 34%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 3-methoxybenzoyl chloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 34% yield; m.p. 75-77° C.; 1H NMR (CDCl3, 300 MHz) δ 7.43-7.31 (m, 8H), 7.12 (td, J=2.4, 6.7 Hz, 1H), 5.97 (t, J=5.6 Hz, 1H), 4.58 (d, J=5.6 Hz, 2H), 3.82 (s, 3H), 2.47 (s, 3H); MS (ES+) m/z 382.1 (M+1).

Sources & evidence

ORD record
ord-67e90ad412c9495b9d57483c574bfd58
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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